


Apps, Boundaries and Carriages

by LiberAmans214



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Bi-Curious Dean Winchester, Biphobia, Castiel Has a Crush on Dean Winchester, Castiel and Dean Winchester Need to Use Their Words, Charlie Bradbury & Dean Winchester Friendship, Dean Winchester Loves The Impala, Eventual Happy Ending, Fluff and Angst, Holding Hands, Homophobia, I'm Bad At Summaries, Internalized Homophobia, John Winchester Being an Asshole, M/M, Online Dating, POV Dean Winchester, Sexuality Crisis, Texting, also pretty fluffy
Language: English
Status: Completed
Published: 2019-05-27
Updated: 2019-05-27
Packaged: 2020-03-20 06:48:46
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,445
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18987442
Author URL: https://archiveofourown.org/users/LiberAmans214/pseuds/LiberAmans214
Summary: Dean meets Castiel online, most thanks to Charlie Bradbury. It is unbelievably easy to fall for him, once they begin to text. But when they decide to actually go out, all of Dean's homophobic upbringing attacks with a vengeance. However, Cas ~ the ever impulsive, the ever romantic ~ suggests a carriage ride, followed by hand holding. And like hell, Dean isn't into it.But it gets even harder when the carriage driver reminds him of John Winchester, because of course it's just gotta get even more tough, until it becomes nearly impossible for Dean to convince Cas that he's very much still into him, because the proudly gay dork doesn't really understand why holding hands on a date is suddenly such a turn-off.





	Apps, Boundaries and Carriages

Dean Winchester doesn’t do ‘online dating’.

But what he can agree to, while sufficiently drunk and  _not_  thinking, is setting up a profile on one of those sites that Charlie says are for gays who aren’t looking to put out on the first date - as long as the Impala is his profile picture.

(They work out a compromise, and  _@impala67_  ends up having Dean on the profile himself, but he’s leaning against the Impala so that’s something.)

Another thing Dean didn’t expect to do was meet men like  _Castiel_  on there. Or find himself looking, for that matter. This time, its far from a compromise when they ‘match’ according to the site programming crap, and end up talking - its more like one of the best things that’s ever happened to him.

He even starts using punctuations and honest to god  _grammar_  in his texts, so that’s saying something.

Castiel Novak is something of a regular in Dean’s head now, and texting him is  _easy_  and  _fun_  and when they talk, sometimes he’s laughing at his screen - and when they flirt, sometimes he ends up red, so that’s how it was. It was good. Cas was awesome, and funny, and smart, and dorky, and sorta into him - and Dean was more pleased than he’d expect.

Until, one average grey evening, after a morning of sparsely talking about zucchini fries and Led Zepp - Cas ups and sends him a ’ _I think we should meet soon’_  with a smiley face, and the lack of snark is a reminder of how serious this is - and Dean is so completely thrown off that he reads the message another seven times and then shoves the phone away instead of replying.

It must be noted, right around this point, that Dean Winchester was still an emotionally repressed, closeted asshole who’d probably never said the word ’ _bisexual_ ’ out loud in general public,  _ever_.

*

He’s made aware, with equal alarm and surprise, of the intensity of his attraction to Cas freakishly soon, because when Cas hesitantly follows it up with a question tag, Dean’s thumbs are rushing to type out the ’ _yes_ ’.

Because, apparently, he thinks they should meet soon,  _too_.

*

Cas insists, coming off as  _happy_ , that he’d make the plans for the date. Dean doesn’t put up much of an opposition to that anyways.

So when Thursday comes along, Dean drives to the largest Starbucks on 4th, where they decided to meet, and waits outside in his car for Cas to show up first - still indecisive and fighting with the resolute voice in his head which asked him to  _ditch_ , and delete Cas’s phone number, and move to Alaska for good measures.

When its three minutes past seven, his sonuvabitch alter-ego is fucking winning. Some part of Dean is making it impossible to get the car in gear and leave - but it’s getting weaker and weaker. Sure, he’s slept around with men and women alike, enough to be assured of his ‘equal preferences’ character - but he hasn’t done this before. Hasn’t been on a motherfucking date with a  _man_. Hasn’t met somebody he’s been texting for almost a month now, at a goddamn Starbucks, for a  _date._ He hasn’t done any of this shit, and he’s freaking out.

But Cas is  _Cas_.

And Dean knows that guy, even though he only has a mental picture of a black-haired Caucasian male to go with it (Cas wasn’t big on descriptions or exchanging selfies anymore than Dean was) and he knows that he’s gonna regret leaving if he does.

So in spite of the fact that it’s probably the wrong decision, Dean for once doesn’t act out in a rush of adrenaline and speed off, but waits.

And then his phone buzzes, and Dean anxiously reads the notification of a new text.

_< << Are you there yet?_

Dean whips his head up to look for Cas, because the message implies that Cas is there already.

_**> >> you at starbucks already?** _

_< << No, but I’m outside_

_Fucking where,_  Dean mutters to himself, looking around even more keenly. He can’t, for the sake of anything, see someone who resembles his mental image of the guy. Suddenly, everyone has blonde hair and everyone has boobs. No one looks like what Dean imagines the source of that magnificent whiskey-over-gravel voice to look like.

He’s a fucking idiot. He should’ve asked for a photo. For a snap of his fucking passport, maybe.

_< << you?_

**_> >> me too_ **

Dean pauses, sucking in a breath. He doesn’t know what to do, and now the voice in his head is getting louder than ever. Perhaps this was a  _sign_  or some of that philosophical  _Universe_  crap.

But now’s too late to bail.

Dean should’ve been more of  _himself_  (an asshole) to Cas, and he wouldn’t have wanted to meet then.  _Screw him_  for bringing out a side of Dean he didn’t know he even had - charming without the disgusting, funny without being obnoxious, interested and not just  _pretending_  to listen for the sake of getting laid.

His thumbs did an anxious dance, hovering over his keyboard, wondering how to tell Cas in the most sane-ish way ever, that he thought that they should depart and continue to text and call for the rest of their goddamn lives, if Cas would have him - but just  _not_  have to be here at this moment.

But just then, there’s a sound, and Dean could get freaking whiplash as he turns, with a yelp.

A sharp tap on his window.

Followed by a man bending to come into Dean’s line of sight through the frosted window - blue eyes and a  _jawline_ , a seven-o'clock shadow and chapped lips - gorgeous and fucking  _black_  hair.

He wore a beige trenchcoat, and his somehow blue eyes were widened in surprise and recognition, though Dean knew they’d never seen each other before - because you don’t forget a man who looks like that. He was tall, judging from how low he bent from his hip, and strongly built. He didn’t say a word but “Dean?”, and  _yep_. It was  _Cas_.

Dean sort of slammed his door against Castiel as he scrambled out - all of his thoughts of running away, fading gradually in the backdrop of  _meeting_  this man. He was face to face, with a man who’d been making him chuckle and blush and stay awake most of the night - and the man apparently had a  _handsome_  fucking face too.

Cas stared back, having to look up a mere inch to meet Dean’s eyes. “Hello, Dean.”

And Dean knew that he wasn’t gonna walk out on this evening, even if Cas’s idea of a good date was  _gardening_.

*

As the evening goes on, Cas’s voice begins to drown out most of Dean’s insecurities.

He’s fully assured in his capability to  _freak_ , and knows that he’ll probably have a passable panic attack the moment he returns to the solitude of his apartment - but at the moment, walking next to Cas, after a lovely dinner at a burger joint - talking and listening and exchanging stories punctuated by private glances; he isn’t really thinking anymore of the fact that he’s on a serious-as-fuck date with a man.

A date that involved dinner, dessert, and now walking. If there was moonlight, and it was a secluded area of the town, it had to be an overlookable event.

Then Cas suddenly turns to him, and his eyes are wide with a new excitement and Dean is intrigued and has to ask. “What, Cas?”

“What are your thoughts on carriages, Dean?” He says, in a voice which is a tad bit softer than his usual baritone.

“Huh?”

“Well,” Cas begins to ramble, and Dean listens with raised eyebrows. “You  _know_ this is  _new_  to me, and I’ve hardly ever dated someone I don’t know like  _you_  - but this is you and here we are, and to say the least, this evening is sort of like a surprise dream for a thirty-one years old nonentity in accountancy like me - and it’s been all comfortable and mellow, but I want a spark -”

“It’s not even been four hours yet, and we’ve lost our spark?” Dean threw back, grinning. Cas rolled his eyes, and shook his head - adorably  _not_  composed for perhaps the first time.

“I mean, its been a good date, but I want this to be more memorable, and I want us to do something spontaneously that’s not just dinner and walks - and for the sake of saying that we did it someday, and I want that we -” Cas paused, breathless. “Am I being weird, Dean?”

“Nah, you’re being sorta cute.” Dean muttered, only loud enough for Cas to hear. “Go on, you want us to do something impulsive, for no reason?” He can’t help but grin. “Like what, Cas?”

And Cas slowly turns his head, deliberating Dean to follow his gaze to the actual  _carriage_  on the road. Its larger than Baby, and has wheels, and is attached to a couple of white horses, and is, all in all, a goddamn carriage.

“So,” Cas mumbled, looking up at him through his eyelashes and making Dean’s chest hurt with the intensity of the throbbing. “What are your thoughts on carriages, Dean?”

*

“This is ridiculous.” Dean declares, after Cas has climbed up after him, and sat down next to Dean, thighs brushing, looking fucking  _pleased_  with the entire situation.

The carriage was goddamn moving. And Dean Winchester was sat in it.

It was a difficult thing to process. Horses were trotting (or doing their cantor thing) and there was a man in a tuxedo sitting a metre in front of them - who’s job was to conduct stupid people like Dean and Cas wherever they want, in his black carriage.

Which looked like it was out of a goddamn storybook.

Dean exchanged a glance with Cas, who’d been steadily beaming at Dean.

“Why?” Dean mouthed, because he didn’t know if he wanted to say anything out loud, since the tuxedo guy in front could hear them clearly.

“Because we’d already walked a long way, and you had to get to your car, to get home.” Cas reasoned, with a grin - and a little part of Dean could roll his eyes but most of him fucking melted because Castiel fucking Novak was adorable, and liked carriages and spoke about what he wanted to do, and needed reassurance that he wasn’t being weird in the middle of a proposal - and made him sit in a real  _carriage_.

Instead, outwardly, Dean blinked twice, and stopped speaking completely.

*

Okay.

So maybe the carriage wasn’t totally a bad thing. There was some fun in the idea of it, if he could get past the terrifying thought of people who knew Dean, seeing him ride a carriage with a man. If he could get past it, there was the whole element of  _freaking awesome._

But the guy driving it (can it be called driving if there isn’t a motor, Dean couldn’t decide) was a real fucking issue.

Dean hadn’t even thought about it, really.

The more he spoke to his passengers - starting from the weather, moving to the Mets - the more they came to know that the guy was a hot-blooded homophobic redneck, who genuinely believed Dean and Cas were platonically riding his carriage as bros hanging out - against the alternative of believing that two (sorta) homosexual men were on a date in this scenario.

Frankly speaking, he felt like a goddamn mirror for Dean’s dad - and he hated it with a passion but it closed him up completely.

The guy even looked largely like John.

Silent to the point of hostile, Dean stared out the carriage. Cas carried on a customary, small-talk conversation which sounded uncomfortable.

“…so that’s what I meant when I said, girls really love these carriages, man.” The man guffawed, and when Cas only politely grinned in response, he was silent for a moment.

Dean’s eyes finally met Cas’s.

Cas looked at him, upset. “Do you want to get off?” He whispered, and before Dean could answer that he didn’t mind the ride, but  _how can you not see the circumstances in which we’re riding this romantic-as-hell thing, Cas -_ the man spoke up himself.

“What, you want to get off?” He asked, peeping at Dean over his shoulder. “Don’t like the speed? You want me to make it go faster, you know you only gotta ask me once, brother.”

“I’m good.” Dean gritted through his teeth, barely meeting Cas’s eyes again.

“Dean,” Cas repeated, imploring. “I’m sorry, and we can  _really_  get off -”

“No, Cas,” Dean snapped. “I’m having a good time.” And it was not bothering him that the driver reminded him of his fucking dad - the infamous John Winchester, who had screwed Dean up in a million different ways, and was the foremost to blame for his current state of closeted asshole-ness, after perhaps himself.

Cas looked disappointed, and Dean hated himself for making the guy frown as upset as that, but he swallowed and let it go.

“You enjoy  _yourself_ , dude.” Dean conjured up the most manly voice he could, unthinking.

And the 'dude’ would probably be replaced by ’ _bro_ ’, if the driver resembled John Winchester anymore than he already did, and  _okay_. This wasn’t a good decision at all. Dean wasn’t ready for this. For any of this.

Alaska was back on the map, and Cas’s eyes flashed with a sensitive vulnerability before turning away.

Awesome. Dean fucking sucked, in more ways than just one.

*

Having an internal identity crisis, combined with the nagging reminder that Cas didn’t do nothing to deserve Dean, and a recurring flashback of John Winchester calling Dean’s first celebrity male crush at eleven  _bullshit_  - plus the fear of accidentally outing himself to a complete stranger who probably walked  _anti_ marches from his manner of speaking of politics and culture - topped off by the sexuality issues Dean eternally festered in; it was not a good evening.

Then suddenly, something happens.

Right at the verge of the driver - Ron, he said his name was - probably asking Cas or Dean about the ladies in their lives or some shit - Dean’s phone buzzed.

Absent minded, Dean picked it up, and skimmed through the 3-word-message twice before looking back up at the sender Cas.

_< << Wanna hold hands?_

Dean gives Cas a look that is supposed to mean a lot of things like,  _I can’t, because I can’t fucking hold hands in public, especially when we’re sitting behind a man who reminds me of my intensely homophobic dad, even though I know I could take him alone if there rose a need to, but I don’t want that, any of the drama, because its too_ hard _, and that’s why, lets not hold hands though I have a feeling that’d feel_ real _good_

But Cas misreads it.

Okay, maybe Dean doesn’t exactly give him the right cue, especially when he moved his hand to an approachable position between both of their laps, and maybe he’s not that good at telling stuff through looks -

Or maybe he didn’t even try to tell him that, and instead went  _yes._

Because Cas is holding Dean’s hand the next moment, stroking the soft skin of the back of his hand with a thumb, even while Dean’s traitorous heart thumps against his chest and butterflies take over his insides. Dean’s hand is enveloped in Cas’s warm one, palm against palm, and the fact that Dean’s sweaty palm is practically clammy and gross, Cas doesn’t budge, and keeps up the stroking rhythm until Dean’s breathing even again.

He looks at Cas with a look which is most definitely supposed to mean  _he doesn’t know we’re gay. Why are you -_

Now Cas is  _clearly_  bad at reading his signs, because he merely gives Dean’s hand a squeeze, and as he relaxes, it’s as if some of the tension settled in Dean’s muscles go away.

Well, at least their hands are invisible when entwined in the dark silhouette of the night.

*

They get down, next to Baby, pretty soon after that. Dean and Cas split the bill, and Ron goes away.

The pit in Dean’s stomach does not.

“Cas,” He whispers, because he’s gonna do it. He’s gonna say it.

“Yes?” Cas smiles.

“I - I ought to tell you, right a-away,” Dean stammers through his hesitations. “There’s a  _reason_  I can’t do this.” Cas’s face falls, but Dean knows he has to go on. “I’m not - I’m not out, Cas. I don’t know if I ever will be. Its just - not a thing on my agenda.”  _I’m a coward. Also, I was raised by John Winchester. I’ve been conditioned to live with it._

Cas looks surprised, which is surprising too. Dean thought he was fucking crystal clear.

“So, I can’t -” He’s supposed to say, he can’t  _date_  him. This is goodbye. “Hold hands.” He finishes, awkward.

“But you just did.”

“Because you -”

“- did I force you to?” Cas looked terrified of Dean’s answer.

Dean leapt to his rescue. “No! That’s because you’re you! And because you texted me - and because I needed to, I dunno what, I just did! But I can’t anymore! Because that guy was - was not  _okay_ with it, and no one is gonna be.”

Its when he says it out loud that he realizes how stupid he sounds.

“So _Ron_  wasn’t okay with you holding my hand.” Cas repeated.

Dean nodded, because he was fresh out of  _words_  for tonight. It was, in fact, uncharacteristic for him to have said as much as he did. It was Dean. Dean didn’t talk about his feelings. He either rode them through, or repressed them so deep that his wise pain-in-the-ass brother too wouldn’t be able to get at them.

So he shut up, and nodded.

“But did you enjoy it?”

Dean didn’t exactly want to lie, so he nodded carefully.

“So, you’re gonna not do something that you enjoyed doing, because Ron - who I believe stands as a mirror for our heteronormative and largely homophobic society - doesn’t want you to.” Cas pronounced, as if it was that simple.

Dean shook his head at first, then opened his mouth to protest, realised Cas was right, and shut up. He even nodded, deliberately slow and not meeting Cas’s eyes.

“I’m not Oprah, Dean,” Cas went on. “But why do you wanna do that to yourself? You don’t think you deserve to be happy by just doing the thing you want to do, in the first place, without bothering for the  _Rons_?”

Dean squirmed. It was a fucking first date. Cas wasn’t his therapist. He knew him pretty well, but he didn’t know the tip of the iceberg when it came to how screwed up his head was. “Just - don’t, Cas.”

“I know what its like, Dean,” Cas threw back, concern in his eyes. “Why would you think I don’t get it?”

_Because you didn’t grow up with John Winchester._

“Can we move on?” Dean dodges. “I’m sorry, okay? I’ll hold hands if you want us to.”

And that’s where he goes wrong, because Cas begins to glare at him. Okay, he did not mean to make it sound like that. He wasn’t doing a favor to Cas by holding his hand, Cas didn’t need him to do anything like that. Cas was speaking for Dean’s good and Dean was being a jerk to him in return.

“I don’t -” He fumbles. “I don’t wanna talk about this! I cannot!”

“Fine.” Cas draws back, eyes narrowed. “I guess I should leave then.”

Dean purses his lips.

_Don’t?_

_Stay_.

_Please_.

“Cas.” Dean says, tired.

“Yes?” He bristles.

_Please don’t stop texting me._

_Maybe we can get back to my apartment and hold hands._

_I want you to stay._

“Can I drop you home?”

“Do you really want to do that right now?” Cas blinked.

“I want to do this.” Dean replied. “But I’m not ready to come out yet, and can you take that?”

Cas hesitates. Dean balks. Then Cas nods. “As long as you allow me to help you through it.”

“I need it,” Dean accepts. “Thank you for respecting my, uh, crap.”

“Boundaries.” Cas prompts.

“I’m sticking with crap.”

*

Dean kisses him off his own free will, outside his apartment, and decides that its  _worth_  working on, if it means getting to hold hands with, and kiss this man all the time - rather than just when alone.

Its gonna be a long journey. Its gonna be complicated and Dean’s gonna fall on his face and flail. But he’s gonna have Cas at his side, and he’s gonna do it.

And its gonna end with him holding hands with Cas, and marching through fucking Kansas proudly.

**Author's Note:**

> Heya, I hope this made for a good read <3 Leave comments behind if you enjoyed, and you can find me [ here! ](https://misha-moose-dean-burger-lover.tumblr.com/)
> 
> Have a great day, happy hellatus, and Keep It Sailing!


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